DE57491C - Process for the preparation of two nitro - $ - naphthylamines - Google Patents
Process for the preparation of two nitro - $ - naphthylaminesInfo
- Publication number
- DE57491C DE57491C DENDAT57491D DE57491DA DE57491C DE 57491 C DE57491 C DE 57491C DE NDAT57491 D DENDAT57491 D DE NDAT57491D DE 57491D A DE57491D A DE 57491DA DE 57491 C DE57491 C DE 57491C
- Authority
- DE
- Germany
- Prior art keywords
- melting point
- sulfuric acid
- filtered
- nitronaphtylamins
- isomers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 nitro - Chemical class 0.000 title description 3
- 238000002844 melting Methods 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 2
- 239000012452 mother liquor Substances 0.000 claims 2
- 230000003472 neutralizing Effects 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 206010021703 Indifference Diseases 0.000 claims 1
- 235000005811 Viola adunca Nutrition 0.000 claims 1
- 240000000358 Viola adunca Species 0.000 claims 1
- 235000013487 Viola odorata Nutrition 0.000 claims 1
- 235000002254 Viola papilionacea Nutrition 0.000 claims 1
- 230000002378 acidificating Effects 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 235000011116 calcium hydroxide Nutrition 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000005712 crystallization Effects 0.000 claims 1
- 229910052602 gypsum Inorganic materials 0.000 claims 1
- 239000010440 gypsum Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims 1
- XSCFKJGIAYKLRV-UHFFFAOYSA-N N-naphthalen-1-ylnitramide Chemical compound C1=CC=C2C(N[N+](=O)[O-])=CC=CC2=C1 XSCFKJGIAYKLRV-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-Nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-Nitrobenzyl alcohol Chemical group OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 1
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical class CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 241000394605 Viola striata Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- TWXTWZIUMCFMSG-UHFFFAOYSA-N nitride(3-) Chemical compound [N-3] TWXTWZIUMCFMSG-UHFFFAOYSA-N 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Fatentirt im Deutschen Reiche vom 25. Juni 1890 ab.Fatentirt in the German Empire from June 25, 1890.
In der Patentschrift No. 30989 ist ein Verfahren beschrieben, nach welchem durch Eintragen der Nitrate primärer aromatischer Amine in stark abgekühlte Schwefelsäure fast ausschliefslich die betreffenden m-Nitroderivate erhalten werden. Es ist in der Beschreibung nur die Darstellung des m - Nitroanilins, m-Nitro-o- und m-Nitro-p-toluidine erwähnt. Indefs bemerkt bereits Friedländer (Fortschr. d. Theerfarbenfabr., S. ,g 31), dafs sich nach jenem Verfahren nicht ausschliefslich die m -Verbindungen bilden.In patent specification no. 30989 describes a method according to which by entering the nitrates of primary aromatic amines in strongly cooled sulfuric acid almost exclusively the relevant m-nitro derivatives are obtained. It's in the description only the representation of m-nitroaniline, m-nitro-o- and m-nitro-p-toluidines are mentioned. Friedländer (Fortschr. D. Theerfarbenfabr., P that method does not exclusively form the m compounds.
Versucht man in gleicher Weise a-Naphtylamin zu nitriren, so ist das Product der Reaction ein schwarzes Harz, aus welchem nur mit Mühe etwa 10 pCt. Nitronaphtylamin isolirt werden können.Try a-naphthylamine in the same way to nitride, the product of the reaction is a black resin, from which only with difficulty about 10 pCt. Nitronaphthylamine can be isolated.
Ganz anders verläuft die Reaction bei dem ß-Naphtylamin. Es bilden sich hierbei zwei Nitronaphtylamine, welche sich vor den bis jetzt bekannten dadurch auszeichnen, dafs die Nitrogruppe auf der einen, die Amidogruppe auf der anderen Seite des Molecüls steht. Die Nitrogruppe nimmt die α-Stellung ein, denn beim Kochen der Diazoverbindungen der neuen Nitronaphthylamine wird a-Nitronaphtalin gebildet. Sie steht in der anderen Kernhälfte, da die durch Reduction zu erhaltenden Naphtylendiamine von den bis jetzt bekannten Naphtylendiaminen (1-2) und (2 · 4) verschieden sind.The reaction proceeds quite differently with β-naphthylamine. Two are formed here Nitronaphthylamines, which distinguish themselves from those known up to now in that the Nitro group on one side, the amido group on the other side of the molecule. the Nitro group assumes the α-position, because when the diazo compounds are boiled the new ones Nitronaphthylamine is formed from a-nitronaphthalene. It is in the other half of the core, as the naphthylenediamines to be obtained by reduction from the heretofore known naphthylenediamines (1-2) and (2 · 4) are different.
Dasjenige Nitronaphtylamin, welches als Hauptproduct der Reaction gebildet wird, giebt ein gelbes schwefelsaures Salz, welches in kaltem Wasser ziemlich schwer löslich ist und sich beim Eingiefsen der Nitrirungsmasse in kaltes Wasser ausscheidet.That nitronaphthylamine which is formed as the main product of the reaction gives a yellow sulfuric acid salt, which is rather sparingly soluble in cold water and separates out when the nitriding mass is poured into cold water.
Die aus diesem Salz dargestellte Base wird nach ein- bis zweimaligem Umkrystallisiren aus Benzol oder Alkohol in schönen, rothen, langen Nadeln vom Schmelzpunkt 143 ° erhalten; ihre Acetylverbindung schmilzt bei 1970. Die Salze werden durch Wasser theilweise dissociirt und die Diazotirung gelingt deswegen nur in stark saurer Lösung. Das durch Kochen der Diazoverbindung mit Wasser erhaltene Nitronaphtol bildet lange gelbe Nadeln vom Schmelzpunkt 1480.The base prepared from this salt is obtained after one or two recrystallization from benzene or alcohol in beautiful, red, long needles with a melting point of 143 °; its acetyl compound melts at 197 ° . The salts are partially dissociated by water, and diazotization is therefore only possible in a strongly acidic solution. The nitronaphtol obtained by boiling the diazo compound with water forms long yellow needles with a melting point of 148 ° .
Das aus diesem Nitronaphtylamin durch Reduction mit Zinn und Salzsäure erhaltene Naphtylendiamin giebt ein in überschüssiger Salzsäure sehr schwer lösliches Salz und wird am besten in dieser Form abgeschieden.That obtained from this nitronaphthylamine by reduction with tin and hydrochloric acid Naphthylenediamine gives a salt which is very sparingly soluble in excess hydrochloric acid and becomes best deposited in this form.
Die Lösung desselben wird durch Eisenchlorid in der Kälte schwach violett gefärbt und giebt beim Kochen damit einen schwarzvioletten Niederschlag. Die freie Base ist ölig; sie liefert eine Acetylverbindung vom Schmelzpunkt 260 ° , welche in Alkohol schwer, in Essigsäure leicht löslich ist.The solution of the same is colored pale violet in the cold by ferric chloride and when boiled it gives a black-violet precipitate. The free base is oily; it provides an acetyl compound with a melting point of 260 °, which is difficult to convert in alcohol Acetic acid is easily soluble.
Durch Sulfiren des Naphtylendiamins mit rauchender Schwefelsäure oder des Sulfats mit überschüssiger Schwefelsäure bei Temperaturen über ioo° bildet sich als Hauptproduct eine in kaltem Wasser schwer lösliche Monosulfosäure, welche aus heifsem Wasser in wasserhaltigen Nadeln krystallisirt, die, mit unge-By sulphuring naphthylenediamine with fuming sulfuric acid or sulphate with Excess sulfuric acid at temperatures above 100 ° is formed as the main product Monosulphonic acid which is sparingly soluble in cold water and which is obtained from hot water in water-containing acids Needles crystallized, which, with un-
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE57491C true DE57491C (en) |
Family
ID=331857
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT57491D Expired - Lifetime DE57491C (en) | Process for the preparation of two nitro - $ - naphthylamines |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE57491C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2790831A (en) * | 1953-06-24 | 1957-04-30 | Goodyear Tire & Rubber | Improvements in nitrating 1-naphthylamine |
-
0
- DE DENDAT57491D patent/DE57491C/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2790831A (en) * | 1953-06-24 | 1957-04-30 | Goodyear Tire & Rubber | Improvements in nitrating 1-naphthylamine |
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